N-tert-butoxycarbonyl-(2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol | 1019848-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-tert-butoxycarbonyl-(2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol
• 英文别名: tert-butyl (2S,3R)-3-hydroxy-2-(hydroxymethyl)-3-methylpiperidine-1-carboxylate
• CAS: 1019848-29-3
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: UIPKNDSGCHOHSD-JOYOIKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-(2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 反应 6.0h， 以84%的产率得到N-tert-butoxycarbonyl-(2R,3R)-3-methyl-3-hydroxypiperidine-2-carboxylic acid
  参考文献：
  名称：

  A Short Enantioselective Synthesis of N-Boc-(2R,3R)-3-Methyl-3-Hydroxypipecolic Acid from Geraniol

  摘要：

  The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.

  DOI：

  10.1021/jo800080t
• 作为产物：
  描述：

  (2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol 、 二碳酸二叔丁酯 以 乙腈 为溶剂， 反应 24.0h， 以68%的产率得到N-tert-butoxycarbonyl-(2S,3R)-3-methyl-3-hydroxypiperidine-2-methanol
  参考文献：
  名称：

  A Short Enantioselective Synthesis of N-Boc-(2R,3R)-3-Methyl-3-Hydroxypipecolic Acid from Geraniol

  摘要：

  The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.

  DOI：

  10.1021/jo800080t

文献信息

• A Short Enantioselective Synthesis of <i>N</i>-Boc-(2<i>R</i>,3<i>R</i>)-3-Methyl-3-Hydroxypipecolic Acid from Geraniol
  作者：Mark C. Noe、Joel M. Hawkins、Sheri L. Snow、Lilli Wolf-Gouveia

  DOI：10.1021/jo800080t

  日期：2008.4.1

  The asymmetric synthesis of (2R,3R)-3-methyl-3-hydroxypipecolic acid, a key intermediate in the synthesis of dual MMP-13/aggrecanase inhibitors, is described. The title compound is prepared in seven steps with an overall yield of 41% starting from geraniol. Key steps in the synthesis include Sharpless asymmetric epoxidation, which establishes the chiral centers, and a one-pot oxidative olefin cleavage/reductive amination sequence that closes the piperidine ring.